US6458503B1ExpiredUtilityA1

Fluorinated aromatic acetal polymers and photosensitive compositions containing such polymers

81
Assignee: KODAK POLYCHROME GRAPHICS LLCPriority: Mar 8, 2001Filed: Mar 8, 2001Granted: Oct 1, 2002
Est. expiryMar 8, 2021(expired)· nominal 20-yr term from priority
Inventors:Stephan J. W. PlatzerPaul A. PerronMelinda Alden
G03F 7/0046C08F 8/18G03F 7/0215
81
PatentIndex Score
22
Cited by
28
References
28
Claims

Abstract

A novel fluorinated aromatic acetal polymer comprises at least one unit of A and at least one unit of B or C, or at least one unit of each of A, B and C and optionally further comprises at least one unit of either D or E or at least one unit of each of D and E, wherein the units A and B and/or C, and optionally D and/or E are linked together by single covalent C—C bonds and have the formulae: wherein R A is H or C 1 -C 11 alky, or an aryl group that does not contain fluorine, and R B and R C are an aryl groups that contain fluorine. The polymer is prepared by reacting a hydrolyzed polyvinyl acetate polymer or copolymer with at least one non-fluorinated aldehyde component, and at least one fluorinated aromatic component. The polymer is useful is preparing a photosensitive composition which comprises at least one diazo resin and at least one such fluorinated aromatic acetal polymer. Such a photosensitive composition may be applied to a support to form an imageable member which may be imaged to form a lithographic printing plates.p

Claims

exact text as granted — not AI-modified
The invention claimed is:  
     
       1. A fluorinated aromatic acetal polymer composition comprising at least one unit of A and at least one unit of either B or C, or at least one unit of each of A, B and C wherein the units A and B or C are linked together by single covalent C—C bonds and have the                    
       formulae: 
       wherein R A  is H, a C 1 -C 11  alkyl group, or an aryl or group that does not contain fluorine, and R B  and R C  are aryl groups that contain fluorine.  
     
     
       2. The composition of  claim 1  wherein: A and B and C are present in the corresponding ratio n 1 :n 2 :n 3 , where n 1 =10-80 mole %, n 2 =0-65 mole %, and n 3 =0-65 mole %. 
     
     
       3. The composition of  claim 1  further comprising at least one unit of either D or E, or at least one unit of each of D and E, wherein the units of A and B and/or C and D and/or E are linked together by single covalent C—C bonds, and wherein D and E have the formulae:                    
     
     
       4. The composition of  claim 3  wherein D and E are present in the corresponding ratio n 4 :n 5  wherein n 4 =0-50 mole % and n 5 =0-20 mole %. 
     
     
       5. The composition of  claim 1 , comprising at least one unit of A and at least one unit of B wherein unit B has the formula:                    
       where each of R 1  and R 2  is independently F, H or an alkyl group. 
     
     
       6. The composition of  claim 5 , wherein R 1  and R 2  are each F. 
     
     
       7. The composition of  claim 1  further comprising at least one acid group having a pKa equal to or less than 11. 
     
     
       8. The composition of  claim 1  further comprising at least one of a photopolymerizable ethylenically unsaturated group and a photocrosslinkable group. 
     
     
       9. The composition of  claim 1  wherein R A  is an aralkyl group that does not contain fluorine. 
     
     
       10. A method of preparing a fluorinated aromatic acetal polymer composition comprising reacting a hydrolyzed polyvinyl acetate polymer or copolymer with at least one non-fluorinated aldehyde component, and at least one fluorinated aromatic component. 
     
     
       11. The method of  claim 10 , wherein the fluorinated aromatic component is selected from the group consisting of one or more of: 4-fluorophenyl isocyanate; 4-fluorobenzaldehyde; 2,3-difluorobenzaldehyde; 2,4-difluorobenzaldehyde; 2,5-difluorobenzaldehyde; 2,6-difluorobenzaldehyde; 3,4-difluorobenzaldehyde; 3,5-difluorobenzaldehyde; 2,3,4-trifluorobenzaldehyde; 2,3,5,6-tetrafluorobenzaldehyde; pentafluorobenzaldehyde; p-trifluoromethylbenzaldehyde; m-(trifluorometh.yl)benzaldehyde; m-(trifluoromethyl)phenyl isocyanate; p-(trifluoromethyl)phenyl isocyanate; 3,5-bis(trifluoromethyl)phenyl isocyanate; 4-(trifluoromethoxy)phenyl isocyanate; and 2-chloro-5-(trifluoromethyl)phenyl isocyanate. 
     
     
       12. The method of  claim 10 , wherein the fluorinated aromatic component is p-trifluoromethyl benzaldehyde. 
     
     
       13. The method of  claim 10 , wherein the non-fluorinated aldehyde component is selected from the group consisting of at least one of an aliphatic aldehyde, an aromatic aldehyde, an aralkylaldehyde and a carboxyl-functional aldehyde. 
     
     
       14. A fluorinated aromatic acetal polymer composition comprising the reaction product of a hydrolyzed polyvinyl acetate polymer or copolymer, at least one non-fluorinated aldehyde component, and at least one fluorinated aromatic component. 
     
     
       15. A photosensitive composition comprising: (1) at least one diazo resin; and (2) at least one fluorinated aromatic acetal polymer composition comprising at least one unit of A and at least one unit of either B or C or at least one unit of each of A, B and C, wherein units A and B and/or C are linked together by single covalent C—C bonds and have the formulae:                    
       wherein R A  is H or C 1 -C 11  alkyl, or an aryl group that does not contain fluorine, and R B  and R C  are aryl groups that contain fluorine. 
     
     
       16. The composition of  claim 15  further comprising at least one unit of either D or E, or at least one unit of each of D and E, wherein D and E have the formulae:                    
     
     
       17. The photosensitive composition of  claim 15 , wherein the fluorinated aromatic acetal polymer composition comprises at least one unit of A and at least one unit of B and unit B has the formula:                    
       where each of R 1  and R 2  is independently F, H or an alkyl group. 
     
     
       18. The photosensitive composition of  claim 17 , wherein R 1  and R 2  are each F. 
     
     
       19. The photosensitive composition of  claim 15 , wherein the diazo resin comprises a condensation product of 3-methoxy-4-diazodiphenylamine sulfate and methoxymethyl-substituted diphenyl ether and salts thereof. 
     
     
       20. The photosensitive composition of  claim 15  wherein R A  is an aralkyl group that does not contain fluorine. 
     
     
       21. The photosensitive composition of  claim 15  further comprising at least one selected from the group consisting of photoinitiator, photosensitizer and combinations thereof. 
     
     
       22. An imageable member comprising: (a) a support; and (b) a photosensitive composition applied to the support, wherein the photosensitive composition comprises: (1) at least one diazo resin; and (2) at least one fluorinated aromatic acetal polymer composition comprising at least one unit of A and at least one unit of either B or C or at least one unit of each of A, B and C wherein units A and B and/or C are linked together by single covalent C—C bonds and have the formulae:                    
       wherein R A  is H or C 1 -C 11  alkyl, or an aryl group that does not contain fluorine and R B  and R C  are aryl groups that contain fluorine. 
     
     
       23. The member of  claim 22  wherein the acetyl polymer composition further comprises at least one unit of either D or E, or at least one unit of each of D and E, wherein D and E have the formulae:                    
     
     
       24. The member of  claim 22 , wherein the fluorinated aromatic acetal polymer composition comprises at least one unit of A and at least one unit of B and unit B has the formula:                    
       where each of R 1  and R 2  is independently F, H or an alkyl group. 
     
     
       25. The member of  claim 24 , wherein R 1  and R 2  are each F. 
     
     
       26. The member of  claim 22 , wherein the diazo resin comprises a condensation product of 3-methoxy-4-diazodiphenylamine sulfate and methoxymethyl-substituted diphenyl ether and salts thereof. 
     
     
       27. The member of  claim 22  wherein the photosensitive composition further comprises at least one selected from the group consisting of photoinitiator, photosensitizer and combinations thereof. 
     
     
       28. The member of  claim 22  wherein R A  is an aralkyl group that does not contain fluorine.

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